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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:09:11 UTC

Update Date

2019-07-23 07:15:27 UTC

HMDB ID

HMDB0060952

Secondary Accession Numbers

HMDB60952

Metabolite Identification

Common Name

2-hydroxyimipramine

Description

2-hydroxyimipramine is a metabolite of imipramine. Imipramine (sold as Antideprin, Deprimin, Deprinol, Depsol, Depsonil, Dynaprin, Eupramin, Imipramil, Irmin, Janimine, Melipramin, Surplix, Tofranil), also known as melipramine, is an antidepressant medication, a tricyclic antidepressant of the dibenzazepine group. Imipramine is mainly used in the treatment of major depression and enuresis (inability to control urination). It has also been evaluated for use in panic disorder. (Wikipedia)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0060952
     RDKit          3D
2-hydroxyimipramine
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.5345   -1.5415   -1.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0201   -1.0466   -0.3198 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0814   -1.1844    0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060    0.3022   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409    1.0146    0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193    0.5913    1.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209    0.5131    0.7025 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    1.6953    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5080    2.8115    0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    4.0637    0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934    4.1695   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    3.0629   -1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    1.8319   -0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    0.7519   -1.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4397   -0.1875   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3339   -1.1125    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6952   -2.4280    0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058   -3.4406    0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1850   -4.7823    0.3255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248   -3.1254    0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -1.7838    0.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0155   -0.7818    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2986   -2.6111   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432   -1.4588   -1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1374   -0.9360   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8617   -1.8762    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5629   -0.1680    0.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977   -1.5035    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9988    0.4526   -1.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5491    0.8799   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0668    2.1069    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8889    0.8738    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0430   -0.2225    2.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    1.3029    2.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    2.7458    1.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895    4.9677    0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3563    5.1603   -0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031    3.1878   -1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2526    0.0878   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7122    1.1415   -1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833    0.3650    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2102   -0.7913   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7191   -2.6792   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1215   -5.0415    0.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244   -3.8464    1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627   -1.5313    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  7  1  0
 13  8  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

458
  Mrv0541 02271201052D          

 22 24  0  0  0  0            999 V2000
    3.8680    0.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4959   -1.6597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -0.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5817    1.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542    1.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2641    2.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4719    2.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1820   -0.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1819   -1.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1777    0.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581    0.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5425    2.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1934    2.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9680    0.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7678    0.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1516    1.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843    1.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4959   -2.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099   -1.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191    1.7364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2 11  1  0  0  0  0
  2 20  1  0  0  0  0
  2 21  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  1  0  0  0  0
  4 12  2  0  0  0  0
  5  9  1  0  0  0  0
  5 13  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 14  2  0  0  0  0
  9 15  2  0  0  0  0
 10 11  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
 19 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060952

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2O/c1-20(2)12-5-13-21-18-7-4-3-6-15(18)8-9-16-14-17(22)10-11-19(16)21/h3-4,6-7,10-11,14,22H,5,8-9,12-13H2,1-2H3

> <INCHI_KEY>
ROTCPJFWLNDKHU-UHFFFAOYSA-N

> <FORMULA>
C19H24N2O

> <MOLECULAR_WEIGHT>
296.4067

> <EXACT_MASS>
296.1888634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.41132183043769

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol

> <ALOGPS_LOGP>
3.83

> <JCHEM_LOGP>
3.795465640795087

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.528949215998052

> <JCHEM_PKA_STRONGEST_BASIC>
9.17621619514565

> <JCHEM_POLAR_SURFACE_AREA>
26.71

> <JCHEM_REFRACTIVITY>
92.58650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060952
     RDKit          3D
2-hydroxyimipramine
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.5345   -1.5415   -1.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0201   -1.0466   -0.3198 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0814   -1.1844    0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060    0.3022   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409    1.0146    0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193    0.5913    1.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209    0.5131    0.7025 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    1.6953    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5080    2.8115    0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    4.0637    0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934    4.1695   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    3.0629   -1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    1.8319   -0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    0.7519   -1.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4397   -0.1875   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3339   -1.1125    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6952   -2.4280    0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058   -3.4406    0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1850   -4.7823    0.3255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248   -3.1254    0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -1.7838    0.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0155   -0.7818    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2986   -2.6111   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432   -1.4588   -1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1374   -0.9360   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8617   -1.8762    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5629   -0.1680    0.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977   -1.5035    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9988    0.4526   -1.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5491    0.8799   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0668    2.1069    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8889    0.8738    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0430   -0.2225    2.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    1.3029    2.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    2.7458    1.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895    4.9677    0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3563    5.1603   -0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031    3.1878   -1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2526    0.0878   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7122    1.1415   -1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833    0.3650    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2102   -0.7913   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7191   -2.6792   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1215   -5.0415    0.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244   -3.8464    1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627   -1.5313    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  7  1  0
 13  8  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 458                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  N   UNK     0       7.220   1.338   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       4.659  -3.098   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.220  -0.141   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.553   1.979   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.888   1.979   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.960   4.577   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.481   4.577   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.882   3.421   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.559   3.421   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.940  -0.880   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.940  -2.359   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.665   0.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.775   0.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.346   3.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.094   3.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.140   1.357   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.300   1.357   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.483   2.859   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.957   2.859   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.659  -4.577   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.378  -2.359   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.529   3.241   0.000  0.00  0.00           O+0
CONECT    1    3    4    5                                                  
CONECT    2   11   20   21                                                  
CONECT    3    1   10                                                       
CONECT    4    1    8   12                                                  
CONECT    5    1    9   13                                                  
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    4    6   14                                                  
CONECT    9    5    7   15                                                  
CONECT   10    3   11                                                       
CONECT   11    2   10                                                       
CONECT   12    4   16                                                       
CONECT   13    5   17                                                       
CONECT   14    8   18                                                       
CONECT   15    9   19                                                       
CONECT   16   12   18                                                       
CONECT   17   13   19                                                       
CONECT   18   14   16                                                       
CONECT   19   15   17   22                                                  
CONECT   20    2                                                            
CONECT   21    2                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060952
HETATM    1  C1  UNL     1       3.534  -1.541  -1.589  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.020  -1.047  -0.320  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.081  -1.184   0.660  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.606   0.302  -0.487  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.041   1.015   0.679  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.819   0.591   1.357  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.421   0.513   0.702  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.063   1.695   0.202  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.508   2.811   0.724  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.958   4.064   0.375  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.993   4.170  -0.521  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.590   3.063  -1.076  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.104   1.832  -0.695  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.882   0.752  -1.355  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.440  -0.187  -0.251  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.334  -1.112   0.159  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.695  -2.428   0.093  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.806  -3.441   0.396  1.00  0.00           C  
HETATM   19  O1  UNL     1      -2.185  -4.782   0.326  1.00  0.00           O  
HETATM   20  C17 UNL     1      -0.525  -3.125   0.773  1.00  0.00           C  
HETATM   21  C18 UNL     1      -0.135  -1.784   0.847  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.016  -0.782   0.549  1.00  0.00           C  
HETATM   23  H1  UNL     1       3.299  -2.611  -1.710  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.643  -1.459  -1.641  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.137  -0.936  -2.416  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.862  -1.876   0.289  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.563  -0.168   0.742  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.698  -1.503   1.653  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.999   0.453  -1.431  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.549   0.880  -0.754  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.067   2.107   0.381  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.889   0.874   1.447  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.043  -0.222   2.119  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.606   1.303   2.262  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.259   2.746   1.411  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.489   4.968   0.813  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.356   5.160  -0.803  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.403   3.188  -1.777  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.253   0.088  -1.979  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.712   1.142  -1.938  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.883   0.365   0.569  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.210  -0.791  -0.770  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.719  -2.679  -0.210  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.121  -5.041   0.051  1.00  0.00           H  
HETATM   45  H23 UNL     1       0.224  -3.846   1.023  1.00  0.00           H  
HETATM   46  H24 UNL     1       0.863  -1.531   1.121  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4
CONECT    3   26   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8   22
CONECT    8    9    9   13
CONECT    9   10   35
CONECT   10   11   11   36
CONECT   11   12   37
CONECT   12   13   13   38
CONECT   13   14
CONECT   14   15   39   40
CONECT   15   16   41   42
CONECT   16   17   17   22
CONECT   17   18   43
CONECT   18   19   20   20
CONECT   19   44
CONECT   20   21   45
CONECT   21   22   22   46
END

HMDB0060952
     RDKit          3D
2-hydroxyimipramine
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.5345   -1.5415   -1.5888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0201   -1.0466   -0.3198 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0814   -1.1844    0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060    0.3022   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409    1.0146    0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193    0.5913    1.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209    0.5131    0.7025 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    1.6953    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5080    2.8115    0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    4.0637    0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934    4.1695   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    3.0629   -1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    1.8319   -0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    0.7519   -1.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4397   -0.1875   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3339   -1.1125    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6952   -2.4280    0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058   -3.4406    0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1850   -4.7823    0.3255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248   -3.1254    0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -1.7838    0.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0155   -0.7818    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2986   -2.6111   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432   -1.4588   -1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1374   -0.9360   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8617   -1.8762    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5629   -0.1680    0.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977   -1.5035    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9988    0.4526   -1.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5491    0.8799   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0668    2.1069    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8889    0.8738    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0430   -0.2225    2.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    1.3029    2.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    2.7458    1.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895    4.9677    0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3563    5.1603   -0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031    3.1878   -1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2526    0.0878   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7122    1.1415   -1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833    0.3650    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2102   -0.7913   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7191   -2.6792   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1215   -5.0415    0.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244   -3.8464    1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627   -1.5313    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22  7  1  0
 13  8  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxyimipramine hydrochloride	HMDB

Chemical Formula

C₁₉H₂₄N₂O

Average Molecular Weight

296.4067

Monoisotopic Molecular Weight

296.1888634

IUPAC Name

2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol

Traditional Name

2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol

CAS Registry Number

Not Available

SMILES

CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12

InChI Identifier

InChI=1S/C19H24N2O/c1-20(2)12-5-13-21-18-7-4-3-6-15(18)8-9-16-14-17(22)10-11-19(16)21/h3-4,6-7,10-11,14,22H,5,8-9,12-13H2,1-2H3

InChI Key

ROTCPJFWLNDKHU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Dibenzazepines

Direct Parent

Dibenzazepines

Alternative Parents

Substituents

Dibenzazepine
Alkyldiarylamine
Tertiary aliphatic/aromatic amine
Azepine
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Amine
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060952)

Organ

Kidney (HMDB: HMDB0060952)
Liver (HMDB: HMDB0060952)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060952)

Cellular substructure

Cytoplasm (HMDB: HMDB0060952)
Membrane (HMDB: HMDB0060952)

Source

Endogenous

Endogenous (HMDB: HMDB0060952)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Imipramine Action Pathway (PathBank: SMP0000422)

Metabolic pathway

Imipramine Metabolism Pathway (PathBank: SMP0000625)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	3.83	ALOGPS
logP	3.8	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	10.53	ChemAxon
pKa (Strongest Basic)	9.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.71 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.59 m³·mol⁻¹	ChemAxon
Polarizability	34.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.899	31661259
DarkChem	[M-H]-	171.319	31661259
DeepCCS	[M-2H]-	196.339	30932474
DeepCCS	[M+Na]+	171.905	30932474
AllCCS	[M+H]+	172.0	32859911
AllCCS	[M+H-H2O]+	168.6	32859911
AllCCS	[M+NH4]+	175.2	32859911
AllCCS	[M+Na]+	176.1	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	180.0	32859911
AllCCS	[M+HCOO]-	179.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.07 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6488 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.54 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	918.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	203.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	83.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	327.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	329.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	772.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	854.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	303.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1070.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	449.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	459.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-hydroxyimipramine	CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12	3695.8	Standard polar	33892256
2-hydroxyimipramine	CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12	2510.7	Standard non polar	33892256
2-hydroxyimipramine	CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12	2527.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-hydroxyimipramine,1TMS,isomer #1	CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C)=CC=C21	2544.8	Semi standard non polar	33892256
2-hydroxyimipramine,1TBDMS,isomer #1	CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	2758.8	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Imipramine Action Pathway		Not Available
Imipramine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

97154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108051

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 2-hydroxyimipramine (HMDB0060952)

MOL for HMDB0060952 (2-hydroxyimipramine)

3D MOL for HMDB0060952 (2-hydroxyimipramine)

3D SDF for HMDB0060952 (2-hydroxyimipramine)

3D-SDF for HMDB0060952 (2-hydroxyimipramine)

PDB for HMDB0060952 (2-hydroxyimipramine)

3D PDB for HMDB0060952 (2-hydroxyimipramine)

SMILES for HMDB0060952 (2-hydroxyimipramine)

INCHI for HMDB0060952 (2-hydroxyimipramine)

Structure for HMDB0060952 (2-hydroxyimipramine)

3D Structure for HMDB0060952 (2-hydroxyimipramine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized